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Rory's First Time	By : janet1987 Category: G through L > Gilmore Girls Views: 25371 -:- Recommendations : 1 -:- Currently Reading : 1
Disclaimer: I do not own Gilmore Girls. I make no money from these stories.

Chapter List
- 1-Rory's First Time
- 1
Lorelai Gilmore wanted to take her daughter’s virginity.
She knew that sentence sounded wrong but she and her daughter did not have your typical mother-daughter relationship. They were a lot closer. More best friends than mother and daughter. Lorelai only pulled out the mother card when she absolutely needed to, which with a kid like Rory was once in a blue moon.
Rory Gilmore had turned eighteen a few weeks ago and Lorelai knew for a fact that her daughter was still a virgin. Sure, she was dating that punk nephew of Luke’s but Lorelai knew that they had never taken it further than making out on the couch.
Lorelai had entertained the idea of taking Rory’s virginity for a few weeks now. The idea came to early one Saturday morning when she went into Rory’s room to have her annual recounting of the story of Rory’s birth and found her daughter lying on top of the covers masturbating. For a split second, Lorelai thought Rory had done this on purpose. She knew that around the same time every birthday that her mother would appear in her room to tell her the story. The idea of Rory purposely putting herself into that position to get caught touching herself is what really cemented the idea in Lorelai’s head.
Lorelai remembered the scene vividly. Rory laid back on the bed with her legs spread wide. Her left hand covered her breast while she pinched and pulled at the stiff nipple. Her right hand was between her legs alternating between rubbing her clit and plunging two fingers into herself. Her eyes were closed as she brought herself closer and closer to an orgasm. Lorelai felt her panties grow damp watching the scene and had to resist the temptation shove her hand down her panties and get herself off then and there. Even thinking of touching herself while watching her daughter masturbate flooded Lorelai with shame. But as soon as she saw Rory experience was looked like a terrific orgasm and heard her soft whimpers of pleasure, all of those thoughts that this was wrong and shameful flew out the window. She wanted to make her daughter feel that good. Plus it had been a long time since she had been with a woman.
Lorelai quickly composed herself and knocked on the door giving Rory enough time to cover herself up. The whole time she recounted the story to Rory the images of Rory fingering herself raced through her mind. She imagined herself helping Rory, teasing her, going down on her, and using her collection of toys to bring her to an orgasm. Lorelai had to quickly excuse herself as the need to touch herself grew even stronger.
Lorelai had taught her daughter that her virginity was something special and it should be taken by someone that she loved. Lorelai thought of herself as that person. She loved Rory and could make sure that Rory’s first time would be unforgettable. She would make sure that Rory was completely cared for and experienced a terrific orgasm for her first time. The thought of that punk of a boyfriend taking her virginity infuriated Lorelai. She wanted to be the one.
There was only the issue of getting Rory to come around to the idea. Which over the past few weeks since Rory’s birthday seemed less and less like a challenge. Lorelai had fucked herself a few times since then, getting herself off on her bed with her fingers or her favorite vibrator. These recent times she noticed Rory watching her, staying right outside the bedroom where she thought she was hidden but Lorelai saw her. The idea of her daughter watching her turned her on even more. She knew she should feel dirty or ashamed that she got off to thoughts of her daughter but for some reason those feelings did not exist.
Lorelai had a way to set her plan into action though. She had a feeling that Rory was having similar thoughts, after all the girl did watch her masturbate a few times, but still she had to treat the situation carefully.
Her first idea was to see how Rory reacted when she started to dress even more proactively. Her recent outfits consisted of her tightest jeans, low-cut shirts, and skin-tight skirts. Rory’s eyes were all over her outfits watching as she bent over and wiggled her ass just to get a reaction. Rory’s reactions to her outfits were definitely exactly what she was going for. Today though her outfit was more provocative consisting of a tank top with no bra and a pair of hot pants.
Lorelai walked into the kitchen, “Good morning,” she said to Rory who was sitting at the kitchen table. She noticed that Rory’s outfit was different from her usual wardrobe choices. Despite the chilly temps outside, Rory had chosen an outfit similar to her mother’s. She had on a very short skirt and low-cut shirt. It was evident that she had also skipped the bra for the day.
Rory smiled, “Good morning.” She leaned across the table giving her mother an impressive view of her cleavage. Lorelai tried her best not to stare.
If only mother and daughter knew that all the same thoughts were running through both their minds.
Rory had thought recently of her virginity. She knew some of her friends had already lost theirs and they all told her about the wonders of sex. She was ready to lose hers. But not to her boyfriend. As wrong as it sounded, she wanted to lose her virginity to her mother. She knew her mother truly loved her and could definitely take care of her. That’s the reason that she started fingering herself at the moment she knew her mother would walk into her room. She wanted to get her mother into the idea of them becoming something more than just friends or mother and daughter. She had also began to question her sexuality recently. She knew it was wrong to fantasize about her mother but she couldn’t help it.
Lorelai fixed a cup of coffee and joined Rory at the coffee table. Her eyes once again fell on Rory’s cleavage. She bit her lip imagining the feel of them in her hands, how it would feel to run her tongue across the nipple and hear Rory whimper in need.
“So um…” Lorelai said shaking the image of Rory topless out of her head, “What are your plans for the day?”
“I thought I would hang around here,” Rory replied.
Lorelai arched an eyebrow, “No plans with Jess? Trouble in paradise?”
“I just want to stick around the house,” Rory said. She gave her mother a smile, “Just spend time with you, we haven’t spent much time together recently.”
“Oh,” Lorelai said flustered by the idea of spending all day around Rory while she was dressed this skimpy but also thrilled by the same idea. “I would love that.” She reached her hand across the table and placed it on top of Rory’s. She squeezed Rory’s hands, “So what do you want to do today?”
“There’s something I want to talk to you about.”
Lorelai noted the serious expression on Rory’s face, one she had seen several times before usually when Rory was talking about school. “You know you can tell me anything sweets.”
“Anything?” Rory asked. “You promise you won’t freak out?”
“I promise.”
Rory cleared her throat. She was going to be bold and just go for it. “I’ve noticed your outfits recently. I mean I know you dress skimpy but lately they’ve been very provocative. I like them. You look great. On my birthday, I know that you watched me touch myself. I wanted you to watch me. I thought of you while touching myself. I’m still a virgin but I want that to change.”
“You know,” Lorelai said playing along, “I’ve seen you watching me too. You’re not very sneaky.”
“I wasn’t trying to be sneaky,” Rory replied. “I like watching you touch yourself. I want you to touch me like that. I want you to take my virginity.”
“Rory,” Lorelai said. She couldn’t believe how brash her daughter was being. She was usually timid and got flustered easily but not right now.
“I’ve thought about it a lot. I thought about it since you first gave me the sex talk. You said I should lose it to someone I love and care about. I don’t want to lose it to Jess, I’m not ready. I do want to lose it to you though,” Rory replied.
“This is wrong,” Lorelai said. She wanted to play the reluctant part just a bit and not give in so easily.
Rory nodded, “I know that but there is not one else that I want to lose it to. I love you and I thought about this and this is what I really want. I love you.”
Lorelai smiled warmly, “I love you too kid.”
“So you’ll do it?” Rory asked with hope in her eyes. “You’ll take my virginity?”
“Are you absolutely positive you want this?” Lorelai inquired.
“100%,” Rory confirmed.
“To be completely honest, I’ve been thinking about this too, since your birthday,” Lorelai replied. She nodded, “So yes I will take your virginity. I just want to do how much you’re comfortable with so I think we should start slow.”
Rory tried to contain her excitement but couldn’t as she got up from the table and jumped into her mother’s lap wrapping her arms around her, “Thank you, thank you, thank you. I love you.”
“Okay, I said we would take this slow so just calm down,” Lorelai told her daughter. “A kiss first.”
Rory bent her head down and met her mother halfway. This kiss started off and passionate as the pair experimented with the idea of kissing one another for the first time. It wasn’t long before Lorelai ran her tongue along Rory’s bottom lip and was granted access as Rory opened her mouth. Lorelai’s tongue massaged Rory’s causing the young girl to moan softly. The kiss quickly escalated both mother and daughter losing themselves in the kiss while their hands explored one another’s bodies. Going very slow might not be an option for long.
Lorelai patted Rory’s thigh motioning for her to get up. She got up and started to walk out of the kitchen, “My room,” she told Rory before disappearing into the living room and up the staircase.
Rory walked into her mother’s room. “I thought you changed your mind for a second.”
Lorelai let out a small laugh, “No I just didn’t think a kitchen table was exactly appropriate for losing your virginity.” She nodded towards the bed, “Lay down,” she ordered. “This is all about you.”
Rory did as she was told and laid down in the middle of the bed. Lorelai hopped on the bed and crawled over to Rory. She bent down and kissed Rory softly before trailing kisses down her neck. Her hands slipped under the hem of Rory’s t-shirt and lifted it over her head.
“Tell me to stop at any time if you get uncomfortable,” Lorelai said. Rory just nodded in response in just a little bit of shock that this was actually happening.
Lorelai’s hands explored Rory’s soft skin, running up and down her sides. She slid her hand over Rory’s breast feeling the nipple harden under her touch. She locked eyes with Rory as she bent her head down and slowly laved with nipple with her tongue.
“Oh God,” Rory moaned softly.
Lorelai gave her other breast the same treatment. She swirled her tongue around the nipple faster spurred on by Rory’s moans and sighs. She spent a few more minutes alternating between breasts licking and sucking discovering exactly what Rory liked. She licked down Rory’s stomach flicking her tongue into Rory’s bellybutton as her hands made work of removing Rory’s skirt.
Lorelai sat up as she pulled the rest of Rory’s skirt down, “No panties?” Lorelai asked. “You are so my daughter.”
Rory giggled. “I learned from you.” She panted softly as her mother’s hands massaged her thighs inching closer and closer to her wet pussy. “Please touch me,” she begged. “Please.”
Lorelai grinned hearing her daughter beg for her touch. She loved hearing her partners beg in bed. She wanted to hear her beg some more. She placed kisses along Rory’s thigh going close but never quite touching her pussy. Rory bucked her hips towards her mother desperate to get some friction.
“Please mommy,” Rory begged, “Touch me.”
Lorelai gave in hearing Rory call her mommy. Something she had not done since she was at least three. She ran a finger along Rory’s bare slit, “Now Rory, I have a strap-on I can use on you but I think I need to work you up to that first. So want do you want me to use my mouth or my fingers?” she asked still rubbing Rory’s slit slowly and teasingly.
“Anything,” Rory sighed. She moaned, “Just please touch me. I need you to touch me.”
Lorelai flicked Rory’s stiff clit with her finger causing the young girl to gasp. “Hmm you’re so wet Rory.” She slid her finger down and pushed at Rory’s entrance, her finger slid in easily. She pumped it in and out. “Is this what you wanted?”
“More,” Rory begged. Her mother fingering her felt way better than any of her masturbatory efforts.
Lorelai bit her lip as she slid in a second finger. She started pumping in and out a little faster. Her thumb brushed against Rory’s clit which caused Rory to reach out and grabbed at the bed sheets. Lorelai smiled watching her normally so pristine daughter hump her hands as she pumped her fingers in and out.
“Oh yes, oh yes,” Rory panted. “That feels so good.”
“I know you’re a virgin but have you ever experimented,” Lorelai asked casually continuing to finger-fuck her daughter. “Have you ever had your pussy licked?”
Rory shook her head. “No,” she struggled to say already feeling an orgasm build up even though they had only been at these for a few minutes. Her mother’s talented fingers were already going to make her cum.
“I think you’ll like this then,” Lorelai said. She bent her head down and flicked Rory’s clit with her tongue. Rory bucked her hips desperate for more. Lorelai added in a third finger as she sucked Rory’s stiff clit into her mouth playing with it with her tongue. Her tongue rolled around it pushing Rory closer and closer to the edge.
“FUCK!” Rory exclaimed as the orgasm broke through her body. She writhed on the bed as her mother continued finger-fucking her and licking her letting her ride out the orgasm to the last possible second.
Once she was sure she had given Rory a half-decent orgasm and allowed her to ride it out, Lorelai withdrew her fingers. She once again locked eyes with Rory as she slid the fingers into her mouth and sucked on them like a lollipop getting every last drop of Rory’s juice off of them.
“How was that?” Lorelai asked leaning over Rory.
“That was…” Rory panted. “Incredible.”
Lorelai giggled, “You said fuck.” She stood up from the bed and slid her hot pants off. They dropped to the floor and she kicked them across the room.
Rory rolled over on the bed and watched as her mother dug through her nightstand, “Are you going to fuck me now?” she asked.
Lorelai pulled out her strap-on panties with an 8-inch dildo attached. She thought she might should use a smaller one for Rory but this is all she had. She stepped into them and crawled back onto the bed. “What do you think?” she asked.
“Spread your legs a little more,” Lorelai ordered as she kneeled in front of Rory. “Good girl.” She placed the tip of the rubber dildo at Rory’s entrance. “Now this may hurt at first but if it hurts too much just tell me to stop.”
Rory nodded, “Okay.”
Lorelai slowly pushed in. She glanced down at Rory who grimaced in pain and she immediately felt bad for hurting her daughter but Rory nodded for her to keep going. Once the dildo was half-way in, Lorelai leaned down and kissed Rory. “You ready?” Rory nodded again.
Lorelai began thrusting slowly in and out every time taking the dildo in just a little bit deeper. After a few minutes, Rory began moaning clearly not in pain anymore. Lorelai picked up the thrusting going a little bit faster.
“Oh fuck,” Lorelai said as she watched the dildo disappear inside her daughter.
“More,” Rory begged. “Harder. Fuck me harder.”
“I don’t want to hurt you,” Lorelai replied keeping a steady pace with her thrusts.
“Just fuck me!” Rory yelled. “Harder and faster. I need you to.”
Lorelai, turned on by her daughter’s almost dominant voice at this point, started thrusting faster. She grabbed Rory’s hips as she thrust into her. The dildo now fully sank into Rory. Lorelai felt a sweat break out on her skin and was suddenly regretting the fact that she still had a shirt on.
“Oh god yes,” Rory moaned loudly. “Oh fuck, fuck, fuck,” she chanted mindlessly. She grasped at the bed-sheets again pulling them closer to her trying to find something to grasp onto. Her hands let go of the sheets as she grasped the headboard behind her pushing herself down onto her mother’s rubber cock.
“Fucking my daughter,” Lorelai growled as she continued to plough faster and faster into her daughter. Their skin slapped together as Lorelai pushed in the rubber dildo as far as it would go. She watched her daughter below her buck her hips lewdly as she dealt with all the pleasure coursing through her body. Lorelai was dealing with pleasure of her own as the clit stimulator on the strap-on did its job.
Rory pondered for just a moment why her mother had a strap-n but judging by the way that she was fucking her made her think that this was not her mother’s first lesbian experience. She made a note to ask her about that later. Right now she was so close to cumming again. She reached up and began to play with her own breasts pinching and pulling at her nipples.
“That’s right,” Lorelai encouraged. “Play with yourself while mommy fucks you. I can’t believe I’m fucking you,” she panted thrusting into Rory rougher.
Rory arched her back as the orgasm hit her by surprise. She had expected to cum soon but not this soon. She cried out giving way to mindless chanting. Above her Lorelai continued to thrust desperate to cum herself. She thrust into Rory rougher than she meant to until the clit stimulator did its job and rewarded her with one hell of an orgasm.
“Fuck yes,” Lorelai cried out as the orgasm raced through her body. She pulled out of Rory and collapsed on the bed beside her. She raised her hips and pulled the strap-on off so she could suck on the dildo. She sucked loving the taste of Rory’s cum on the dildo.
Coming down from her orgasm, Rory turned to her mother, “Thank you.”
Lorelai gave the dildo one last good lick and dropped it down beside her, “Anything for you babe.”
Rory raised up on her elbows, “Does this have to be just a one-time thing though?”
Lorelai smiled. She would be happy to fuck Rory anytime she asked. She could teach Rory all her tips and tricks for when Rory fucked her. She could also teach her the joy of sex when it came to men, if Rory wanted that. Perhaps they could even share a man if they found a willing one, “If you don’t want it to be a one-time thing, it doesn’t have to be a one-time thing.”
“I don’t want it to be a one-time thing,” Rory replied.
“Then I have a lot to teach you young one.”
- 1
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Rory's First Time